Because I couldn’t possibly cover it all in a newspaper piece, I sent him some follow-up questions by e-mail. Here are my questions and his responses:

DQW: So, how in the world does a guy who dreamed of acting on Broadway and in soap operas become a DEA agent? You spent seven years in New York perfecting your acting skills. Did that training help you as an agent? You have mentioned that it gave you insight into people’s characters.

Milione: I never dreamt of acting in soap operas – but did work on the “boards” in New York and hoped to break into film work. It was all with the goal of being able to work steadily and support my young family at the time. Most of the work I did in the mid-’80s and early ’90s was in professional theater, and my training (Circle in the Square Theater School and subsequently the Actor’s Studio) involved studying/working on many great playwrights (Tennessee Williams, Arthur Miller, Anton Chekhov, Clifford Odets, Eric Overmyer, etc.). What always struck me working on those plays was how wonderfully complex their characters were written and how accurately they reflected real life, exposing the complex “gray” areas in most people. In federal, state or local law enforcement, you’re dealing with people from a broad spectrum: witnesses, sources and defendants. All are very complex and interesting human beings. When you focus on a target in any investigation, it certainly is important to know as much about them as possible and to understand (to the best of our ability) what motivates them so that we can be safer and more effective during the investigation.

Not everyone thought you could bring down Bout. In fact, one government official told you that there was no way you could lure him out of Russia, where he had avoided capture for years. What made you think you could be successful? And why were you targeting an arms dealer? You work for the DEA. Explain the nexus between drugs and arms trafficking, if you don’t mind.

Drug Trafficking Organizations (DTOs) are the epitome of “transnational criminal organizations.” They operate domestically and internationally. They are fast moving and flexible in their business structure, and they work with arms traffickers, money launderers, corruptors, assassins, terrorists and others to accomplish their goals. These “shadow facilitators” are the engine behind drug traffickers. Viktor Bout falls in that “shadow facilitator” category. DEA had information about Bout and potential links to the FARC [a rebel group in Colombia that the U.S. has designated a terror organization] and other groups. We began the investigation, followed the evidence as it developed, and then the prosecutors in the United States Attorney’s Office in the Southern District of New York reviewed it, making the appropriate charging decisions. Drug traffickers, narco-terrorists, arms traffickers, terrorists, money launderers, etc. don’t place themselves in specific categories. They all work together to accomplish their goals. DEA has seen this for decades and has had a long history of proactively investigating sophisticated “transnational criminals” that have been characterized as untouchable. My confidence sprang from previous successful, similar investigations we have done and with the knowledge of DEA’s unique capabilities in the foreign arena where DEA has 84 offices in 65 countries. In these locations, extremely capable DEA agents work operationally with trusted foreign counterparts and make investigations like this one possible.

Were you nervous when Bout couldn’t meet you guys in Bucharest and you had to leave town, possibly killing the deal? Explain the risks/rewards in that decision.

We were all nervous but believed the decision was the right one. At that point in the investigation, we knew Bout was trying to come to Bucharest for the meetings but also knew he had concerns about going. His efforts were confirmed from telephone wiretaps in Bucharest that were approved by a Romanian judge. These intercepts gave us the comfort that Bout was making every effort to get to Bucharest. We had to balance waiting for Bout and playing the “scenario” as realistically as possible. To play it realistically, we had to let Bout know we had other “business” to attend to in other international locations. Waiting too long for Bout to try and get into Bucharest would have looked strange and desperate, which could plant doubt about the undercovers in Bout’s mind. That is something we wanted to avoid at all cost. Walking away at that moment was calculated to look believable and gave us the time to prepare for our next move, which was to arrange a meeting with him in another location (Thailand).

What was your reaction when you heard that Bout had landed in Bangkok to meet with your informants? A federal grand jury in New York had indicted him. So you could grab him if you wanted to. It must have been a relief?

The knot in our collective stomachs went from a triple knot to maybe a double knot. It was a huge relief but we knew we still had a distance to go yet. A number of us (DEA and Thai counterparts) were staging in a hotel room waiting for that call. Other DEA agents and Thai counterparts were conducting surveillance at the airport. When the call came in that Bout and his associate landed, we knew this was moving forward and we all breathed a little easier.

When Bout reached into his briefcase instead of putting up his hands, was there a moment when you thought, “Oh, no, ‘The Merchant of Death’ isn’t going to die in a prison. He’s going to be killed right here!’ ”

I didn’t think in those terms. However, I did observe that the Thai police intensified their commands to Bout in English and focused their weapons more keenly on Bout when Bout hesitated upon our entry into the undercover conference room. I wondered what Bout was going to do when he heard that command. I had a very good idea of what the Thai police were going to do if Bout didn’t comply quickly. We aren’t focused on having someone “die in prison.” We do the investigation … work with all our partners … bring the case and the defendant into an open U.S. court and then if the defendant chooses, go to trial, where everyday citizens listen to the evidence and decide guilt or innocence. Whether convicted or acquitted, none of this is personal. It’s only business.

This investigation started at your offices in Northern Virginia and involved a ruse involving a Colombian rebel group seeking weapons from a Russian arms trafficker. Then it stretched undercover meetings in the Caribbean island of Curacao — bet you enjoyed that part of the sting — then to Copenhagen, Romania and finally Thailand. Obviously, you don’t rush into these investigations without carefully planning. But how do you manage a sting spread across so many countries and involving so many different characters and back stories? Is it different than running a drug investigation targeting a murderous D.C. street gang, for example?

I haven’t worked drug investigations in D.C. but can relate it to my time working them in New York City. There are plenty of parallels. Both types of investigation are often proactive and fast-moving; both types of investigations have periods of adrenaline and hours/days of waiting. Domestic drug trafficking groups, especially violent ones, rely on criminals that supply weapons, assassins, transporters, money launderers and other criminal specialties. While the Bout investigation involved multiple countries and a larger geographic area, domestic investigations also may involve multiple cities, states and/or certain foreign countries. The basic approach to the investigation is still the same: Identify the threat, infiltrate the group, gather the evidence, team with great prosecutors, indict, arrest, prosecute. Managing all the different aspects in the Bout investigation was easy because of the quality of all the agents, analysts, prosecutors and foreign counterparts.

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